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jtorrrresFlag for United States of America

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SBS 2008 to Office 365

I am in the process of performing a cutover migration for email from SBS 2008 to Office 365. I have Autodiscover and SSL cert working great. There are 2 email domain names being used in the on-premise server and both domains have been verified in O365. The users that use '', have a separate mailbox. In other words, user 'Bob' has mailbox '' & '' (Single Domain SSL cert, SRV Autodiscover)

Despite O365 detecting the mailboxes for '' to migrate, when it attempts to do so, an error is generated. "The cloud-based service failed to detect connection settings using Autodiscover. Please specify the connection settings manually or go back to the first step and retry using Autodiscover." Migration for '' is working fine and is currently migrating.

It seems obvious that although the connection is successful to the on-premise Exchange server using '' connection settings, when it attempts to migrate mailboxes on the same server with '', that the migration tool is checking '' for Autodiscover settings.

Here is my questions:

1) Is this project doable given the circumstances?

2) Will I need to purchase a UCC cert and replace the current single domain cert to add (,, etc)

3) Will adding an Autodiscover SRV record for with a target of, do the job? Since this is the simplest method to try, I have already submitted this change and waiting for it to take effect.

Thanks for the help
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